WO2021222321A1 - Revêtement par pulvérisation antimicrobien, antiviral, à base de cellulose - Google Patents

Revêtement par pulvérisation antimicrobien, antiviral, à base de cellulose Download PDF

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Publication number
WO2021222321A1
WO2021222321A1 PCT/US2021/029491 US2021029491W WO2021222321A1 WO 2021222321 A1 WO2021222321 A1 WO 2021222321A1 US 2021029491 W US2021029491 W US 2021029491W WO 2021222321 A1 WO2021222321 A1 WO 2021222321A1
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WO
WIPO (PCT)
Prior art keywords
microbial
viral
layer
coating
cellulose
Prior art date
Application number
PCT/US2021/029491
Other languages
English (en)
Inventor
Soma Shekar Dachavaram
John P. Moore
Peter A. Crooks
Jamie Hestekin
Original Assignee
Board Of Trustees Of The University Of Arkansas
Bioventures, Llc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Board Of Trustees Of The University Of Arkansas, Bioventures, Llc filed Critical Board Of Trustees Of The University Of Arkansas
Priority to US17/921,955 priority Critical patent/US20230174814A1/en
Publication of WO2021222321A1 publication Critical patent/WO2021222321A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D101/00—Coating compositions based on cellulose, modified cellulose, or cellulose derivatives
    • C09D101/02—Cellulose; Modified cellulose
    • C09D101/04—Oxycellulose; Hydrocellulose
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0058—Biocides

Definitions

  • cellulose nanomaterial are hydrophilic by nature, which makes them a poor moisture barrier. It has been seen that certain compounds can be added to create composite coatings and thereby increasing the hydrophobic properties of OTO-CNMs.
  • One such class of compound is alkyl ketene dimers (AKD), which not only increases the hydrophobicity of the cellulose films but helps to maintain their eco-friendly properties as well.
  • ALD alkyl ketene dimers
  • Another limiting factor of cellulose nanomaterial is that the films produced tend to break down in the water, which makes them a poor barrier in wet environments. It has been seen that certain compounds can be added to bind cellulose materials together and thereby increasing the physical stability of OTO-CNM films in a wet environment.
  • One such class of compound known as a cross-linking agent binds together compounds on a molecular level, such as glutaraldehyde.
  • Another such type of compound is a non toxic ionic liquid, 1 -Ethyl-3 -methylimidazolium acetate, which not only increases the stability of the cellulose films but maintains their eco-friendly properties as well.
  • the present invention provides a spray-on surface that can be anti-viral and anti-bacterial to stop the spread of infectious disease.
  • the present invention provides different techniques for achieving spray-on tunability.
  • the present invention provides an innovative way to improve and administer OTO-CNMs, and environmentally friendly composites thereof, as a gas and moisture barrier for coating and packing various consumer goods.
  • the present invention uses tosyl cellulose as an intermediate to create various anti-microbial surfaces directly on cellulose, namely Ciprofloxacin, Sulfamethoxazole, Trimethoprim, Isoniazid, Metronidazole, and Daptomycin.
  • the present invention uses a binding agent to stabilize or strengthen the film.
  • the present invention uses a cross-linking agent as the binding agent.
  • the present invention uses an ionic liquid as the binding/cross-linking agent.
  • the present invention for food packaging applications, provides clear, edible moisture barriers.
  • the present invention provides materials to decrease food spoilage, maintain freshness, be sustainable, and that is ingestible by humans.
  • the present invention provides material having a complex nanoscale structure.
  • the present invention provides methods to produce water-stable films. [00019] In other embodiments, the present invention provides methods to assemble cellulose into nanorods and nanoparticles that are less than 20 nanometers in length. [00020] In other embodiments, for hemodialysis applications, the present invention provides optically clear filters that increase flow-through and cause less fouling. Testing of the present invention shows that the cellulose material allows more blood to flow through a specific area in less time and with less fouling of blood on the membrane.
  • the present invention provides transparent membranes that increase ion transport in electrodialysis, electro deionization, and reverse electro deionization with particular emphasis potassium selectivity.
  • the present invention provides an edible moisture barrier via dip coating and spray coating methods.
  • the material is biocompatible, biodegradable, and can be produced sustainably.
  • the present invention provides anti-microbial and anti bacterial small molecules attached to the cellulose surface spray coatings.
  • the present invention provides coatings having the ability to stop the spread of a virus by killing various viruses and bacteria, which includes Escherichia coli, Staphylococcus aureus, and COVID-19.
  • the present invention provides cellulose-bound anti microbial agents for use in the biomedical field for wound dressing in debridement protocols after traumatic bone and tissue injury, as well as to seal and sterilize an area from the environment for prolonged periods in high contact locations in public places.
  • the present invention provides surface food packaging materials for food preservation and for maintaining contamination integrity both at the point of the farm as well as upon arrival at the point of sale. Materials can include a dye or non-toxic color agent to indicate the efficacy of the material.
  • the present invention provides a spray-on surface that can be anti-viral and anti-bacterial that may be used to stop the spread of infectious disease.
  • This cellulose-based coating may be used to improve and administer 0T0- CNMs and environmentally friendly composites thereof, as a gas and moisture barrier for packaging various consumer goods.
  • the spray can be produced as a liquid to be aerosolized, or it can come prepacked as a pressurized aerosol can. The goal is to provide a quick-drying surface coating material that can easily be handled and applied by both large companies and consumers.
  • the present invention uses a combination of cellulose and an edible wax to tune hydrophilicity.
  • the present invention uses and does not use a combination of cellulose and surfactant.
  • the present invention uses a surfactant (Tween-19) in dilute concentrations ( ⁇ 0.1%) to facilitate the spreading and even consistency of the cellulose coating.
  • the present invention provides a spray-on packaging that attaches to surfaces.
  • a cellulose surface may be formed that is anti-viral and can be modified to spray on surfaces. Because of these properties, it is an ideal coating for keeping surfaces virus/bacteria-free.
  • FIG. 1 illustrates nitrogen permeance of uncoated, dip coated, and spray coated 4% Form I gas barrier coatings on PVDF supports produced tested under ASTM E 2178 standards for air gas permeability.
  • Figure 2 illustrates air, nitrogen, carbon dioxide, and oxygen permeance, (L/s/m2) at 75 pascals, of dip and spray coated 4% CNM gas barrier coatings on PVDF supports tested under ASTM E 2178 standards for gas permeability.
  • Figure 3 illustrates air permeance of spray coated 4% OTO-CNM as represented by mass percent of Form II within the solution used for the gas barrier coatings produced tested under ASTM E 2178 standards for gas permeability.
  • Figure 4 illustrates contact Angle Graph and Images for embodiments of the present invention.
  • Figure 5 are SEM Imaging of for embodiments of the present invention with frontal and cross section views as well as the thickness of each cellulose coating.
  • Figure 6 illustrates synthesized various quaternary ammonium celluloses for an embodiment of the present invention.
  • Figure 7A illustrates cellulose-bound antimicrobial agents, using tosyl cellulose as an intermediate for an embodiment of the present invention.
  • Figure 7B illustrates cellulose-bound antimicrobial agents, using tosyl cellulose as an intermediate for an embodiment of the present invention.
  • Figure 8 illustrates antimicrobial agent using Daptomycin for an embodiment of the present invention.
  • Figure 9 illustrates click chemistry reaction route for embodiments of the present invention.
  • Figure 10 shows tribological information pertaining to the number of rubs the material can have before breaking or rubbing off (SS is stainless steel) for an embodiment of the present invention.
  • Figure 11 illustrates HNMR of cellulose ammonium salt in D20 for an embodiment of the present invention.
  • Figure 12 illustrates C-NMR of cellulose ammonium salt in D20 for an embodiment of the present invention.
  • Figure 13 illustrates dilution plates from Phi6 exposed to Fl+HTA coating on a stainless steel carrier for 2 hours. Coating was allowed to rest for 24 Hours at STP before exposure.
  • Figure 14 illustrates controls: (Left) Direct plating of Phi 6 stock. (Right) Fifth dilution of Phi 6 stock. This shows presence of Phi 6 virus. Sixth serial dilution resulted in 70 CFU, equating to 7 *10 L 8 CFU/ml for stock.
  • Figure 15 shows Form 1 + Myristyltrimethylammonium (C14 chain length).
  • Figure 16 Form 1 + Hexadecyl trimethyl ammonium (C16 chain length).
  • Figure 17 shows an embodiment of the present invention applied to a substrate such as a door handle for an embodiment of the present invention.
  • the present invention provides thin-film composites that may be formed by a layer-by-layer deposition (i.e., dipping) of polymer materials. Dip and spray deliver the application benefits of the two vastly different OTO- CNMs to be exploited. Dip and spray coating may be used in the development of a thin film to take advantage of shear stress on particles within a solution to create a uniform layer on a substrate.
  • Various concentrations of OTO-CNM Form I, OTO-CNM Form II, and AKD wax is used in the preparation of a four percent by weight aqueous cellulose solution.
  • a spray jet is used to apply the cellulose nanomaterial and AKD wax to the substrate. Depending on the solutions, the jet is run in a range of 15 to 30 psi. Both sides of the substrate are coated to prevent excess wrinkles. Samples are placed first in a Petri dish, and the Petri dishes is then placed in a nitrogen-filled dry box for several hours until dry. The coated samples are put into a Millipore dead-end membrane apparatus.
  • a gas flow pressure meter is used to measure the transmembrane pressure (TMP) and SLPM passing through the sample. The system is run at several TMPs, and their respective standard liter per minute or SLPMs are collected. TMPs and SLPMs are then used to calculate the gas transfer rate normalized to ASTM E 2178 - 03 standards.
  • the units for comparison are standardized based on temperature, pressure, and molecular weight of the gas used for the analysis. This unit is known as the standard liter per minute or SLPM. Furthermore, it is essential to be able to normalize air permeance to recognized values. Therefore, the ASTM E 2178 standards for gas permeability were chosen.
  • the ASTM standard is the permeance (L/s/m2) at 75 pascals.
  • SLPM is then converted to units of permeance (L/s/m2) at 75 pascals, as dictated by ASTM E 2178.
  • the values are calculated from several data points at different pressure for each membrane. Triplicate samples were run using nitrogen as the test gas. The averages of those their membranes where 7.62 x 10-4 (L/s/m2) at 75 pascals for the dipping method and 4.96 x 10-5 (L/s/m2) at 75 pascals for the spraying method.
  • the spray technique provides a significant improvement over the dipping method, with a 175% percent difference in the gas barrier.
  • Figures 1-4 show how various embodiments serve as membranes or barriers. While little to no separation between gases was observed, it was more important to be able to adjust the amount of gas that could permeate through the membrane. While Form I coatings exhibited the ability to act as a gas barrier, Form II coatings were shown to be feeble gas barriers. Form II can be used as a pore-forming agent to control the porosity of the Form I coat, showing that tunability among the gas barrier properties is possible and has been achieved.
  • anti-bacterial/viral coating 110 may be applied to a substrate 100 which may be a door pull such as a handle or knob.
  • small anti-bacterial/viral molecules may be attached to cellulose products as shown in Figures 7-9.
  • the coating may be obtained by incorporating anti microbial species either through covalent bonding to or via non-covalent interaction with the surface of cellulose polymers.
  • tosyl cellulose may be used as an intermediate.
  • PVDF Polyvinyl difluoride
  • SEM shows the total covering of the PVDF surface using the substrate of choice, i.e., Form I (as shown in Figure 15), Form II (as shown in Figure 16), and AKD wax composite.
  • AKD wax is applied in conjunction with Form I, binding of the wax to the cellulose substrate occurs. It was observed that Form I has better gas barrier properties and that this could be attributed to the dense matrix that develops as seen by SEM.
  • Form II forms spotty, porous structures that do not create gas barriers on the surface but provide other beneficial properties such as hydrophilicity or pore formation for gas tunability.
  • Form I + AKD show the binding of the wax to the CNM substrate while maintaining the dense film needed for a gas barrier material.
  • a click chemistry reaction route can be utilized in the synthesis of Form 1 covalently bonded antifungals, anti-bacterial agents, anti-viral, and anti- MRSA/antiseptic agents.
  • Most agents fall into three categories: Benzalkonium chlorides (quaternary ammonium compounds), Hydrogen peroxide-based compounds (peroxyacetic acid usually).
  • the cellulose ammonium salt could be characterized by solution-state 1-H and C-13 NMR in D2O due to its water-solubility.
  • the moisture barrier properties may be further enhanced by increasing the concentration of AKD wax and other secondary materials that have been known to increase hydrophobicity.
  • covalent and ionic modifications of the cellulose may provide various alternative uses of the surface-modified cellulose besides just for the packaging.
  • a colored dye (less than 5% concentration) may be included in the composite spray material so that when sprayed on a surface such as a doorknob, someone would know that it is safe to touch as long as the knob remains colored with the dye. Furthermore, when the surface starts returning to its original color, the exterior can be resprayed, and anti-viral activity restored.
  • a surfactant i.e., tween-19 at 0.0155 concentration
  • tween-19 at 0.0155 concentration may be included in the composite spray material so that when sprayed on a surface such as a doorknob coating consistency and spreading could be maximized.
  • the coating can be applied without a surfactant and still be valid.
  • the simple addition of a binding agent may be included in the form of a cross-linking agent such as an ionic liquid in the composition of less than one percent in the composite spray material so that when sprayed on a surface such as a doorknob, it would be water-stable as long as the knob coating wasn’t physically removed.
  • a cross-linking agent such as an ionic liquid in the composition of less than one percent in the composite spray material so that when sprayed on a surface such as a doorknob, it would be water-stable as long as the knob coating wasn’t physically removed.
  • a binding agent may be the solvent in the form of a cross-linking agent such as an ionic liquid in the composition of 90% binding agent 10 % cellulose by mass.
  • a cross-linking agent such as an ionic liquid in the composition of 90% binding agent 10 % cellulose by mass.
  • the dissolved cellulose solutions can then be regenerated in a water bath to produce non-toxic freestanding cellulose films.
  • non-toxic freestanding cellulose films can be prepared between 100-2000 microns for hemofiltration applications.
  • non-toxic freestanding cellulose films can be prepared at 200 microns for hemofiltration showed nominal loss of performance over long term fouling studies with blood and bovine serum albumin.
  • non-toxic freestanding cellulose films can be prepared between 100-2000 microns for ion separation applications, including deionization, electro deionization, reverse electro deionizaton.
  • non-toxic freestanding cellulose films can be prepared at 750 microns for ion separation applications where potassium selectivity is essential. These membranes have shown potassium ion selectivities of greater than 99%.
  • two quantanry ammonium based coatings were tested for antiviral efficacy against Pseudomonas virus phi6. Testing followed EPA Protocol for the Evaluation of Bactericidal Activity of Hard,Non- porous Copper Containing Surface Products.
  • Coating A was made from Form 1 Tempo- Oxidized cellulose (Form 1) and Hexadecyl trimethyl Ammonium (HTA).
  • Coating B was made from Form 1 and Myristyltirmethyl Ammonium (MTA). Coatings were of 5000 relative ppm. Each coating was tested on stanless steel and brass carrier substrates.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Nanotechnology (AREA)
  • Plant Pathology (AREA)
  • Composite Materials (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
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Abstract

L'invention concerne un revêtement anti-viral/antimicrobien à base de cellulose.
PCT/US2021/029491 2020-04-27 2021-04-27 Revêtement par pulvérisation antimicrobien, antiviral, à base de cellulose WO2021222321A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US17/921,955 US20230174814A1 (en) 2020-04-27 2021-04-27 Cellulose Based Anti-Viral Anti-Microbial Spray Coating

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202063016161P 2020-04-27 2020-04-27
US63/016,161 2020-04-27

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WO2021222321A1 true WO2021222321A1 (fr) 2021-11-04

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WO (1) WO2021222321A1 (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070104758A1 (en) * 2004-06-16 2007-05-10 Paul Hamilton Biofunctional, antimicrobial coatings for medical devices
US20090035342A1 (en) * 2004-07-30 2009-02-05 Karandikar Bhalchandra M Antimicrobial Devices and Compositions
US20090182337A1 (en) * 2006-05-15 2009-07-16 Stopek Joshua B Antimicrobial Coatings
US20110177145A1 (en) * 2009-07-27 2011-07-21 E.I. Du Pont De Nemours And Company In situ preparation of peracid-based removable antimicrobial coating compositions and methods of use
US20150010715A1 (en) * 2004-04-29 2015-01-08 Bacterin Antimicrobial coating for inhibition of bacterial adhesion and biofilm formation
US20160346436A1 (en) * 2013-06-20 2016-12-01 The Governors Of The University Of Alberta Nanocrystalline cellulose hydrogels for inhibition of bacterial adhesion
WO2019026071A1 (fr) * 2017-07-30 2019-02-07 IMI Tami Institute for Research and Development ltd Matériau de revêtement antimicrobien comprenant de la cellulose nanocristalline et de l'oxyde de magnésium et son procédé de préparation

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150010715A1 (en) * 2004-04-29 2015-01-08 Bacterin Antimicrobial coating for inhibition of bacterial adhesion and biofilm formation
US20070104758A1 (en) * 2004-06-16 2007-05-10 Paul Hamilton Biofunctional, antimicrobial coatings for medical devices
US20090035342A1 (en) * 2004-07-30 2009-02-05 Karandikar Bhalchandra M Antimicrobial Devices and Compositions
US20090182337A1 (en) * 2006-05-15 2009-07-16 Stopek Joshua B Antimicrobial Coatings
US20110177145A1 (en) * 2009-07-27 2011-07-21 E.I. Du Pont De Nemours And Company In situ preparation of peracid-based removable antimicrobial coating compositions and methods of use
US20160346436A1 (en) * 2013-06-20 2016-12-01 The Governors Of The University Of Alberta Nanocrystalline cellulose hydrogels for inhibition of bacterial adhesion
WO2019026071A1 (fr) * 2017-07-30 2019-02-07 IMI Tami Institute for Research and Development ltd Matériau de revêtement antimicrobien comprenant de la cellulose nanocristalline et de l'oxyde de magnésium et son procédé de préparation

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BIESER ARNO M., THOMANN YI, TILLER JOERG C.: "Contact-Active Antimicrobial and Potentially Self-Polishing Coatings Based on Cellulose : Contact-Active Antimicrobial and Potentially Self-Polishing …", MACROMOLECULAR BIOSCIENCE, WILEY-VCH VERLAG GMBH, DE, vol. 11, no. 1, 10 January 2011 (2011-01-10), DE , pages 111 - 121, XP055869421, ISSN: 1616-5187, DOI: 10.1002/mabi.201000306 *
BIESER ARNO M., TILLER JOERG C.: "Mechanistic Considerations on Contact-Active Antimicrobial Surfaces with Controlled Functional Group Densities : Mechanistic Considerations on Contact-Active Antimicrobial …", MACROMOLECULAR BIOSCIENCE, WILEY-VCH VERLAG GMBH, DE, vol. 11, no. 4, 8 April 2011 (2011-04-08), DE , pages 526 - 534, XP055869424, ISSN: 1616-5187, DOI: 10.1002/mabi.201000398 *

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